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- W2055476957 abstract "Carbocyclic nucleosides have received much attention due to their interesting biological activity and metabolic stability. Among nucleoside analogues, a fluorine substitution on the carbohydrate moiety or introduction of a 2‘,3‘-unsaturated structure motif has been proven to be successful in producing effective antiviral agents. By combining these structural features, both d- and l-2‘,3‘-dideoxy-2‘,3‘-didehydro-2‘-fluoro-carbocyclic nucleosides (d- and l-2‘F-C-d4Ns) were synthesized as potential anti-HIV agents. The target d- and l-carbocyclic nucleosides were both stereospecifically synthesized from d-ribose. The structure−activity relationships of synthesized compounds against HIV-1 in activated human peripheral blood mononuclear (PBM) cells were studied, from which we found that the l-2‘,3‘-dideoxy-2‘3‘-didehydro-2‘-fluoroadenosine analogue (l-2‘F-C-d4A) 46 showed potent anti-HIV activity (EC50 = 0.77 μM), although it is cross-resistant to the lamivudine-resistant variant (HIV-1M184V). Modeling studies demonstrated a good correlation between calculated relative binding energies and activity/resistance data. The modeling study also indicated that an additional hydrogen bond and a favorable van der Waals interaction contribute to the higher antiviral activity of l-2‘F-C-d4A in comparison to its d-counterpart. Also, like other l-nucleosides, the unfavorable steric hindrance of the sugar moiety of l-2‘F-C-d4A and the side chain of Val184 could explain the cross-resistance of l-2‘F-C-d4A with the M184V mutant. The significant difference of antiviral activity between carbovir and its analogue l-2‘F-C-d4G 25 may be due to distortion of the phenyl ring of Tyr115 in the l-2‘F-C-d4G-TP/HIV-RT complex, which resulted in a poor π−π interaction." @default.
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- W2055476957 date "2005-05-03" @default.
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- W2055476957 title "Synthesis, Antiviral Activity, and Mechanism of Drug Resistance of <scp>d</scp>- and <scp>l</scp>-2‘,3‘-Didehydro-2‘,3‘-dideoxy-2‘-fluorocarbocyclic Nucleosides" @default.
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- W2055476957 doi "https://doi.org/10.1021/jm050096d" @default.
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